With the rise of nationalism and the current contentious debate on immigration in the US, school leaders and educators are faced with difficult questions about how to negotiate sensitive political topics, including debates on immigration. In this article, Reva Jaffe-Walter, Chandler Patton Miranda, and Stacey J. Lee explore how educators grapple with the political policies and discourses surrounding immigration with marginalized students who are the subject of those politics. Drawing on research from two US schools exclusively serving recently arrived immigrant students, the authors explore how educators negotiate the teaching of immigration politics during two different time periods, in 2013 during the Obama era "Dreamer" movement and in early 2017 after the inauguration of Donald Trump. They consider how the unique conditions of each political context inform educators' strategies for "teaching into" political events and supporting their immigrant and undocumented students. Their analysis reveals the unique challenges of engaging marginalized students who are the subject of contentious politics in political discussion and action and supports their call for a deeper consideration of students' identities and experiences of politics within scholarly discussions of critical civic engagement.